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Chemical Structure| 108649-59-8 Chemical Structure| 108649-59-8

Structure of 108649-59-8

Chemical Structure| 108649-59-8

1-(2-Bromoethyl)-2,4-dichlorobenzene

CAS No.: 108649-59-8

4.5 *For Research Use Only !

Cat. No.: A368694 Purity: 95%

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Product Details of [ 108649-59-8 ]

CAS No. :108649-59-8
Formula : C8H7BrCl2
M.W : 253.95
SMILES Code : ClC1=CC=C(CCBr)C(Cl)=C1
MDL No. :MFCD07369774
InChI Key :BJTSTVKJPXWNIY-UHFFFAOYSA-N
Pubchem ID :10848510

Safety of [ 108649-59-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H318-H413
Precautionary Statements:P280-P301+P310-P305+P351+P338
Class:8(6.1)
UN#:2922
Packing Group:

Application In Synthesis of [ 108649-59-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 108649-59-8 ]

[ 108649-59-8 ] Synthesis Path-Downstream   1~31

  • 1
  • [ 288-88-0 ]
  • [ 108649-59-8 ]
  • 1-<2-(2,4-dichlorophenyl)ethyl>-1,2,4-triazole [ No CAS ]
  • 2
  • [ 108649-59-8 ]
  • [ 10387-40-3 ]
  • [ 1028279-93-7 ]
  • 3
  • [ 81156-68-5 ]
  • [ 108649-59-8 ]
  • 4
  • [ 108649-59-8 ]
  • [ 1028264-17-6 ]
  • 5
  • [ 108649-59-8 ]
  • [ 1026752-86-2 ]
  • 6
  • [ 108649-59-8 ]
  • 2-[2-(2,4-Dichloro-phenyl)-ethylsulfanylmethyl]-2-hydroxy-succinic acid [ No CAS ]
  • 8
  • [ 108649-59-8 ]
  • [ 711017-43-5 ]
YieldReaction ConditionsOperation in experiment
1- (2-BROMOETHYL)-2, 4-CHLOROBENZENE * (6.8g) was mixed with sodium sulphite (3.36g) in a 4: 1 mixture of water : dioxan (50MI) and heated to 140C overnight. A further 25ML of dioxan was added and reflux continued for a further 24 hours.. The mixture was then cooled to room temperature and concentrated in vacuo. The residue was triturated with diethyl ether and dried to give the title compound. RT 3.68min [M-Na] + 253. * Sharafian et AL., J. Het. Chem. 1994,31, 6,1421
  • 9
  • [ 536-75-4 ]
  • [ 108649-59-8 ]
  • [ 129254-90-6 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 9 Preparation of 1-(2,4-dichlorophenyl)-3-(4-pyridyl)butane 1.0 g (9.35 mmol) of 4-ethylpyridine and 2.37 g (9.35 mmol) of <strong>[108649-59-8]2,4-dichlorophenethyl bromide</strong> were reacted in the same manner as in Example 1. The reaction product was purified to obtain 0.67 g of the desired compound (yield: 25.6%). The resulting compound was identified as 1-(2,4-dichlorophenyl)-3-(4-pyridyl)-butane (hereinafter referred to as compound 9) by the following analytical results.
  • 10
  • [ 95-92-1 ]
  • [ 108649-59-8 ]
  • C12H12Cl2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: Magnesium turnings (13.2 g, 0.55 mol) were placed in dry THF (25 mL) undernitrogen. A small amount (10 mL) of (2-bromoethyl)benzene (92.5 g, 0.50 mol) dissolvedin dry THF (300 mL), added to the magnesium slurry and stirred for a few minutes withwarming until the reaction commenced. The remainder of the (2-bromoethyl)benzenesolution was added dropwise to maintain reflux over an hour, then the reaction mixturewas aged at reflux for an additional an hour. The reaction mixture was cooled to 25 C. In a separate flask, diethyl oxalate (88.2 g, 0.6 mol) was dissolved in dry THF (100mL) and cooled to -10 C. The supernatant solution of (2-phenylethyl)magnesiumbromide was sucked under nitrogen through a sintered-glass filter into a dropping funnel.The reaction temperature was held at -10 C as the solution of Grignard reagent wasadded dropwise over an hour to the diethyl oxalate. The sintered-glass funnel anddropping funnel were then rinsed with dry THF (100 mL), and the rinse was added to thebatch. The reaction mixture was allowed to stand for 30 min and then quenched byaddition of 3 M HCl (145 mL).Hexane (500 mL) was added, and the aqueous layer was discarded. The organicphase was washed with brine (100 mL) and saturated NaHCO3 (100 mL), until theaqueous layer measured to pH 5.0. The organic phase was dried with anhydrous Na2SO4.Filtered and washed with hexane, and the combined layers were concentrated to an oil invacuum. The crude keto ester (103.0 g) was vacuum distilled at 105-110 C (0.2-0.3 mmHg) to afford a colourless oil 90.0 g with 60% yield.
  • 11
  • [ 108649-59-8 ]
  • [ 1058856-50-0 ]
  • 12
  • [ 108649-59-8 ]
  • [ 1327337-56-3 ]
  • 13
  • [ 108649-59-8 ]
  • [ 1260521-21-8 ]
  • 14
  • [ 110-86-1 ]
  • [ 108649-59-8 ]
  • [ 1360869-10-8 ]
YieldReaction ConditionsOperation in experiment
at 140℃;Neat (no solvent); General procedure: Pyridine or 4-picoline (1 mmol) and phenylalkyl halide derivatives (1.2 mmol) were condensed at 140 C to yield the corresponding N-phenylalkyl pyridinium halides.refPreviewPlaceHolder26 W. Wichitnithad, T.J. McManus and P.S. Callery. Rapid Commun. Mass Spectrom., 24 (2010), p. 2547. [26] and refPreviewPlaceHolder[47] The products were solidified from diethyl ether. Sodium borohydride (5 mmol) was added in portions to a stirred solution of the N-phenylalkyl pyridinium halide (1 mmol) in 30 mL of dry methanol at 0 C. The mixture was stirred for an additional 4 h, and the solvent was subsequently removed under reduced pressure. The residue in 30 mL of water was extracted with ethyl acetate (3 × 20 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated to near dryness under reduced pressure. The crude tetrahydropyridine was purified by column chromatography on silica using 1% triethylamine in hexane/ethyl acetate (1:5). The obtained product was eluted through a basic alumina column with CH2Cl2 to yield the corresponding N-phenylalkyl substituted 1,2,3,6-tetrahydro-pyridine, which was converted to the hydrochloride salt by dissolving the free base in 10 mL of 120 mM ethanolic HCl and evaporating to afford pure tetrahydropyridine hydrochloride.
  • 15
  • [ 108649-59-8 ]
  • [ 1351938-86-7 ]
  • 16
  • [ 108649-59-8 ]
  • [ 1351938-92-5 ]
  • 17
  • [ 108649-59-8 ]
  • [ 15128-90-2 ]
  • [ 1355026-31-1 ]
  • 18
  • [ 108649-59-8 ]
  • [ 1443040-00-3 ]
YieldReaction ConditionsOperation in experiment
93% With sodium azide; In N,N-dimethyl-formamide; at 60℃; for 10h; To a solution of <strong>[108649-59-8]2,4-dichlorophenethylbromide</strong> (1 g, 698 muL, 3.96 mmol) in 80 mL of anhydrous DMF, sodium azyde (523 mg, 7.9 mmol) was added and the mixture was stirred at 60 C for 10h. EtOAc (50mL) were added and washed with water (3 x 25 mL) and brine (3 x 25 mL). The organic layer wasdried with MgSO4 and concentrated under reduced pressure to give a yellow liquid (798 mg, 3.67mmol, 93%)
  • 19
  • [ 108649-59-8 ]
  • [ 1443040-02-5 ]
  • 20
  • [ 108649-59-8 ]
  • [ 1443040-03-6 ]
  • 21
  • [ 108649-59-8 ]
  • 1-(2’,4’-dichlorophenylethyl)-5-formyl-1H-1,2,3-triazole [ No CAS ]
  • 22
  • [ 108649-59-8 ]
  • 1-(2’,4’-dichlorophenylethyl)-5-hydroxymethyl-1H-1,2,3-triazole [ No CAS ]
  • 23
  • [ 1012040-38-8 ]
  • [ 108649-59-8 ]
  • 2-(2,4-dichlorophenylethyl)-4-hydroxymethyl-1H-1,2,3-triazole [ No CAS ]
  • 24
  • [ 104-92-7 ]
  • [ 108649-59-8 ]
  • [ 1578261-43-4 ]
  • 25
  • [ 104-92-7 ]
  • [ 108649-59-8 ]
  • 1-[2-(2,4-Dichloro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-1H-imidazole [ No CAS ]
  • 26
  • [ 288-32-4 ]
  • [ 108649-59-8 ]
  • [ 61019-61-2 ]
YieldReaction ConditionsOperation in experiment
45% Under a nitrogen atmosphere, a mixture of imidazole (2.1mmol, 2.1eq) and K2CO3 (1mmol, 1eq) in dry THF (6mL) was stirred at room temperature for 10min. A solution of <strong>[108649-59-8]1-(2-bromoethyl)-2,4-dichlorobenzene</strong> (3a, 1mmol, 1eq) in THF (1mL) was added, and the mixture was heated under reflux for 14h. The solution was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in CH2Cl2, and the solution was washed with water (5mL, twice). The CH2Cl2 layer was extracted with dilute aqueous HCl (5mL, three times). The aqueous extract was neutralized with solid NaHCO3, and the free base was extracted using CH2Cl2 (10mL, three times). The combined organic extracts were dried (Na2SO4) and concentrated. High-vacuum drying gave 4a as an oil in 45% yield. 1H NMR (400MHz, CDCl3): delta 7.44-7.42 (m, 1H), 7.33 (s, 1H), 7.14 (dd, 1H, J=8.2, J=2.2Hz), 7.05 (bs, 1H), 6.88 (d, 1H, J=8.0Hz), 6.85 (s, 1H), 4.20 (t, 2H, J=7.0Hz), 3.16 (t, 2H, J=7.0Hz) ppm.
  • 27
  • [ 108649-59-8 ]
  • [ 365996-07-2 ]
  • 2-bromo-5-(2,4-dichlorophenethyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
38.2% With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 60℃; for 6h; Step i: Synthesis of 2-bromo-5-(2,4-dichlorophenethyl)-4,5,6 ,7-tetrahvdrothiazolo[5,4-clpyridine A mixture of l-(2-bromoethyl)-2,4-dichlorobenzene (0.1 g, 0.000393 mol) and 2-bromo-4,5,6,7- tetrahydrothiazolo[5,4-c]pyridine(0.103 g, 0.000472 mol) in DMF (2 mL) was cooled to 0 - 5 C, and added NaH (0.014 g, 0.00059 mol). The RM was then warmed to 60 C for 6 h. The RM was cooled to RT, quenched with water, extracted into ethyl acetate and organic portion was washed with water, dried over sodium sulphate, concentrated to get the titled compound (0.06g, 38.2%).
  • 28
  • [ 108649-59-8 ]
  • [ 365996-07-2 ]
  • N-(5-(2,4-dichlorophenethyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)-2-(4-(ethylsulfonyl)phenyl)acetamide [ No CAS ]
  • 29
  • [ 4602-73-7 ]
  • [ 108649-59-8 ]
  • [ 1426260-53-8 ]
YieldReaction ConditionsOperation in experiment
74% General procedure: Table 3 is a parameter table. The starting material "parameter 1" was added into a flask at room temperature under N2, and then the "parameter 2" mL IPA and "parameter 3" were added thereinto. The starting material was dissolved at "parameter 4" C. The appearances of reaction solution were "parameter 5" and "parameter 7" in about "parameter 6" minutes, and then the solution was heated at 110~120C for "parameter 8" hours and concentrated in room temperature. The "parameter 9" mL MeOH was added and the resulting mixture was stirred for "parameter 10" minutes. To the solution, which is "parameter 1 1" in a ice-bath, NaBH4(s) "parameter 12" was added slowly under N 2 and stirred for "parameter 13" minutes. The solution, which is "parameter 14," was added with "parameter 15" mL H2O and extracted with "parameter 16" mL CHC13. The organic layer was added with MgS04 for drying, stirred for "parameter 17" minutes, filtered, and concentrated to obtain "parameter 18". The "parameter 20" was afforded after flash column chromatography (silica gel, "parameter 19").
  • 30
  • [ 4602-73-7 ]
  • [ 108649-59-8 ]
  • [ 1426260-73-2 ]
  • 31
  • [ 512-56-1 ]
  • [ 108649-59-8 ]
  • 2,4-dichloro-1-(2-(methylsulfonyl)ethyl)benzene [ No CAS ]
 

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